Mechanochemical synthesis of magnesium-based carbon nucleophiles in air and their use in organic synthesis

Rina Takahashi, Anqi Hu, Pan Gao, Yunpeng Gao, Yadong Pang, Tamae Seo, Julong Jiang, Satoshi Maeda, Hikaru Takaya, Koji Kubota () and Hajime Ito ()
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Rina Takahashi: Hokkaido University
Anqi Hu: Hokkaido University
Pan Gao: Hokkaido University
Yunpeng Gao: Hokkaido University
Yadong Pang: Hokkaido University
Tamae Seo: Hokkaido University
Julong Jiang: Hokkaido University
Satoshi Maeda: Hokkaido University
Hikaru Takaya: Kyoto University, Gokasho, Uji
Koji Kubota: Hokkaido University
Hajime Ito: Hokkaido University

Nature Communications, 2021, vol. 12, issue 1, 1-10

Abstract: Abstract Since the discovery of Grignard reagents in 1900, the nucleophilic addition of magnesium-based carbon nucleophiles to various electrophiles has become one of the most powerful, versatile, and well-established methods for the formation of carbon−carbon bonds in organic synthesis. Grignard reagents are typically prepared via reactions between organic halides and magnesium metal in a solvent. However, this method usually requires the use of dry organic solvents, long reaction times, strict control of the reaction temperature, and inert-gas-line techniques. Despite the utility of Grignard reagents, these requirements still represent major drawbacks from both an environmental and an economic perspective, and often cause reproducibility problems. Here, we report the general mechanochemical synthesis of magnesium-based carbon nucleophiles (Grignard reagents in paste form) in air using a ball milling technique. These nucleophiles can be used directly for one-pot nucleophilic addition reactions with various electrophiles and nickel-catalyzed cross-coupling reactions under solvent-free conditions.

Date: 2021
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DOI: 10.1038/s41467-021-26962-w

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